EP4095124A1 - Arylaminverbindung und organisches elektrolumineszenzelement - Google Patents

Arylaminverbindung und organisches elektrolumineszenzelement Download PDF

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EP4095124A1
EP4095124A1 EP21744716.8A EP21744716A EP4095124A1 EP 4095124 A1 EP4095124 A1 EP 4095124A1 EP 21744716 A EP21744716 A EP 21744716A EP 4095124 A1 EP4095124 A1 EP 4095124A1
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group
substituted
compound
unsubstituted
organic
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French (fr)
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EP4095124A4 (de
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Kouki Kase
Takeshi Yamamoto
Jae-Geon Lim
Junichi IZUMIDA
Shuichi Hayashi
Norimasa Yokoyama
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Hodogaya Chemical Co Ltd
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Hodogaya Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present invention relates to a compound suitable for an organic electroluminescence device (abbreviated hereinbelow as "organic EL device”) which is a self-luminous light-emitting device suitable for various display devices, and to such an organic EL device. More specifically, the present invention relates to an arylamine compound, and to an organic EL device employing the compound.
  • organic EL device organic electroluminescence device
  • Organic EL devices which are self-luminous light-emitting devices, are brighter, have better visibility, and are capable of clearer display compared to liquid crystal devices. Therefore, organic EL devices have been actively researched.
  • C. W. Tang et al. of Eastman Kodak Company developed a device having a multilayer structure wherein various roles for light emission were allotted respectively to different materials, thereby achieving practical utilization of organic EL devices using organic materials. They developed a laminate including a layer of a fluorescent substance capable of transporting electrons and a layer of an organic substance capable of transporting holes. Injecting both charges into the fluorescent substance layer causes emission of light, achieving a high luminance of 1,000 cd/m 2 or higher at a voltage of 10 V or less (see, for example, Patent Literatures 1 and 2).
  • Non-Patent Literature 1 An electroluminescent device wherein an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are formed sequentially on a substrate, achieving high efficiency and high durability (see, for example, Non-Patent Literature 1).
  • Non-Patent Literature 2 To further improve luminous efficiency, attempts have been made to employ triplet excitons. Also, the use of phosphorescent compounds has been investigated (see, for example, Non-Patent Literature 2). Further, devices employing light emission by thermally activated delayed fluorescence (TADF) have been developed. In 2011, Adachi et al. of Kyushu University achieved an external quantum efficiency of 5.3% with a device using a thermally activated delayed fluorescence material (see, for example, Non-Patent Literature 3).
  • TADF thermally activated delayed fluorescence
  • Alight-emitting layer can be prepared by doping a charge-transporting compound, typically called a "host material", with a fluorescent compound, a phosphorescent compound, or a material emitting delayed fluorescence.
  • a charge-transporting compound typically called a "host material”
  • a fluorescent compound typically called a fluorescent compound
  • a phosphorescent compound typically called a fluorescent compound
  • a material emitting delayed fluorescence typically called a fluorescent compound, a phosphorescent compound, or a material emitting delayed fluorescence.
  • the material's heat resistance and amorphous properties are also important. With a material having poor heat resistance, thermal decomposition and material degradation occur, even at low temperatures caused by heat produced when the device is driven. With a material having poor amorphous properties, a thin film undergoes crystallization in a short time, resulting in device degradation. Thus, the material to be used requires high heat resistance and good amorphous properties.
  • Examples of hole-transporting materials used heretofore in organic EL devices include N,N'-diphenyl-N,N'-di( ⁇ -naphthyl)-benzidine (“NPD”) and various aromatic amine derivatives (see, for example, Patent Literatures 1 and 2).
  • NPD N,N'-diphenyl-N,N'-di( ⁇ -naphthyl)-benzidine
  • Tg glass transition point
  • This may cause degradation in device properties due to crystallization in high-temperature conditions (see, for example, Non-Patent Literature 4).
  • Patent Literatures 1 and 2 there are compounds having excellent mobility, such as hole mobility of 10 -3 cm 2 /Vs or greater (see, for example, Patent Literatures 1 and 2). These compounds, however, have insufficient electron blockability, thus allowing a portion of the electrons to pass through the light-emitting layer and thereby making it impossible to expect improvements in luminous efficiency. To achieve even higher efficiency, there is a demand for a material having higher electron blockability and higher heat resistance and providing a more stable thin film. Further, aromatic amine derivatives having high durability have been reported (see, for example, Patent Literature 3), but these compounds are used as charge-transporting materials to be used in electrophotographic photoreceptors, and have never been used in organic EL devices.
  • arylamine compounds having a substituted carbazole structure or a triarylbenzene structure have been proposed as compounds having improved properties such as heat resistance and hole injectability (see, for example, Patent Literatures 4 and 5).
  • Devices using these compounds for the hole injection layer or hole transport layer are improved in terms of device life and luminous efficiency, but these improvements are still insufficient, and there are further demands for even lower driving voltage, higher luminous efficiency, and longer device life.
  • An objective of the present invention is to provide, as a material for highly-efficient highly-durable organic EL devices, a material for organic EL devices which has: (1) excellent hole injectability and transportability; (2) electron blockability; (3) high stability in a thin-film state; and (4) excellent durability.
  • Another objective of the present invention is to provide, by using the present material, an organic EL device which has: (1) high luminous efficiency and power efficiency; (2) a low emission start voltage and practical driving voltage; and (3) a long lifetime.
  • arylamine compounds having a triarylbenzene structure have excellent hole injectability and transportability, thin film stability, and durability, and diligently studied these compounds to pursue optimization and improvement in substitution positions, thereby achieving a material having dramatically improved properties.
  • Inventors have also found that the use of this material in an organic EL device can improve performance in luminous efficiency and power efficiency, suppress emission start voltage and practical driving voltage, and achieve longer lifetime surpassing conventional lifetime, to thus accomplish the present invention.
  • aromatic hydrocarbon group "aromatic heterocyclic group” or “fused polycyclic aromatic group” in the "substituted or unsubstituted aromatic hydrocarbon group", “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted fused polycyclic aromatic group” as represented by Ar 1 to Ar 4 in the general formula (1) may include, for example, aryl groups having 6 to 30 carbon atoms and hetero aryl groups having 2 to 20 carbon atoms, such as a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group, a spirobifluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a trip
  • substituted aromatic hydrocarbon group may include: a deuterium atom; a cyano group; a nitro group; halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; silyl groups, such as a trimethylsilyl group, triphenylsilyl group, etc.; linear or branched alkyl groups having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, etc.; linear or branched alkyloxy groups having 1 to 6 carbon atoms, such as a methyloxy group, an ethyloxy group, a propyloxy group, etc.; alkenyl groups, such as
  • substituents may further be substituted by any of the substituents given as examples above. Further, the aforementioned substituent(s) and the substituted benzene ring, or a plurality of substituents substituting the same benzene ring, may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom, to form a ring.
  • Examples of the "divalent aromatic hydrocarbon group", “divalent aromatic heterocyclic group” or “divalent fused polycyclic aromatic group” in the "divalent substituted or unsubstituted aromatic hydrocarbon group", “divalent substituted or unsubstituted aromatic heterocyclic group” or “divalent substituted or unsubstituted fused polycyclic aromatic group” as represented by L 1 and L 2 in the general formula (1) may include groups similar to divalent groups obtained by removing one hydrogen atom from the aforementioned examples given for the "aromatic hydrocarbon group", “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the "substituted or unsubstituted aromatic hydrocarbon group", “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted fused polycyclic aromatic group” as represented by Ar 1 to Ar 4 in the general formula (1).
  • Examples of the "substituent" in the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted fused polycyclic aromatic group” as represented by L 1 and L 2 in the general formula (1) may include the aforementioned examples given for the "substituent” in the "substituted aromatic hydrocarbon group", “substituted aromatic heterocyclic group” or “substituted fused polycyclic aromatic group” as represented by Ar 1 to Ar 4 in the general formula (1), and they may take similar forms/configurations as those described above.
  • the aforementioned group(s) and the substituted benzene ring, or a plurality of these groups substituting the same benzene ring, may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom, or a sulfur atom, to form a ring.
  • Examples of the "substituent" in the "linear or branched alkyl group having 1 to 6 carbon atoms and optionally having a substituent", "cycloalkyl group having 5 to 10 carbon atoms and optionally having a substituent” or “linear or branched alkenyl group having 2 to 6 carbon atoms and optionally having a substituent” as represented by R 1 to R 7 in the general formula (1) may include the aforementioned examples given for the "substituent" in the "substituted aromatic hydrocarbon group", “substituted aromatic heterocyclic group” or “substituted fused polycyclic aromatic group” as represented by Ar 1 to Ar 4 in the general formula (1), and they may take similar forms/configurations as those described above.
  • the aforementioned group(s) and the substituted benzene ring, or a plurality of these groups substituting the same benzene ring, may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted amino group, an oxygen atom, or a sulfur atom, to form a ring.
  • Examples of the "substituent" in the "linear or branched alkyloxy group having 1 to 6 carbon atoms and optionally having a substituent” or “cycloalkyloxy group having 5 to 10 carbon atoms and optionally having a substituent” as represented by R 1 to R 7 in the general formula (1) may include the aforementioned examples given for the "substituent” in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group” or “substituted fused polycyclic aromatic group” as represented by Ar 1 to Ar 4 in the general formula (1), and they may take similar forms/configurations as those described above.
  • Examples of the "aromatic hydrocarbon group”, “aromatic heterocyclic group”, or “fused polycyclic aromatic group” in the "substituted or unsubstituted aromatic hydrocarbon group", “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted fused polycyclic aromatic group” as represented by R 1 to R 7 in the general formula (1) may include the aforementioned examples given for the "aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted fused polycyclic aromatic group” as represented by Ar 1 to Ar 4 in the general formula (1).
  • Examples of the "substituent" in the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted fused polycyclic aromatic group” as represented by R 1 to R 7 in the general formula (1) may include the aforementioned examples given for the "substituent” in the "substituted aromatic hydrocarbon group", “substituted aromatic heterocyclic group” or “substituted fused polycyclic aromatic group” as represented by Ar 1 to Ar 4 in the general formula (1), and they may take similar forms/configurations as those described above.
  • Ar 1 to Ar 4 in the general formula (1) may preferably be a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group or a spirobifluorenyl group, which may be substituted or unsubstituted, and more preferably a phenyl group, a biphenyl group, a naphthyl group or a phenanthrenyl group, which may be substituted or unsubstituted.
  • Ar 3 and Ar 4 may preferably be a phenyl group or a naphthyl group, which may be substituted or unsubstituted, and more preferably, Ar 3 and Ar 4 are the same.
  • Ar 1 and Ar 2 may preferably be a phenyl group, a biphenyl group, a naphthyl group or a phenanthrenyl group, or a group having a structure in which two groups selected from the above are bonded, and Ar 3 and Ar 4 may preferably be a phenyl group.
  • the sum of integers m and n in the general formula (1) may preferably be 0 or 1, and more preferably, m may be 0 or 1, and n may be 0.
  • Examples of L 1 and L 2 in the general formula (1) wherein m and n are not 0 may preferably be a phenylene group, a biphenylene group or a naphthalene group, which may be substituted or unsubstituted, and more preferably an unsubstituted phenylene group or naphthalene group.
  • R 1 to R 7 in the general formula (1) may preferably be a hydrogen atom or a deuterium atom, or a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group or a spirobifluorenyl group, which may be substituted or unsubstituted, and more preferably a hydrogen atom, a deuterium atom, or an unsubstituted phenyl group, biphenyl group or naphthyl group.
  • R 1 and R 3 may preferably be a hydrogen atom or a deuterium atom
  • R 2 may preferably be a hydrogen atom or a deuterium atom, or a phenyl group, a biphenylyl group, a naphthyl group, a phenanthrenyl group or a fluorenyl group, which may be substituted or unsubstituted.
  • Ar 3 , Ar 4 , and R 2 are preferably the same.
  • R 1 , R 3 , R 4 , R 5 , R 6 , and R 7 may preferably be a hydrogen atom or a deuterium atom
  • R 2 may preferably be a phenyl group.
  • the arylamine compound represented by the aforementioned general formula (1) which is suitably usable for an organic EL device according to the present invention, can preferably be used as a constituent material of a hole injection layer, a hole transport layer, an electron blocking layer, or a light-emitting layer of the organic EL device, and can more preferably be used as a constituent material of a hole transport layer or an electron blocking layer.
  • the arylamine compound of the present invention Compared to conventional hole-transporting materials, the arylamine compound of the present invention has various properties, such as (1) good hole injectability, (2) high hole mobility, (3) excellent electron blockability, (4) high electron tolerance, (5) stability in a thin-film state, and (6) excellent heat resistance.
  • various properties can be achieved, such as (7) high luminous efficiency, (8) a low emission start voltage, (9) a low practical driving voltage, and (10) a long lifetime.
  • the arylamine compound of the present invention has excellent hole injectability and transportability, thin film stability, and durability.
  • an organic EL device having a hole injection layer and/or hole transport layer produced by using the present compound as a hole-injecting material and/or hole-transporting material is improved in hole-transporting efficiency to the light-emitting layer and is thus improved in luminous efficiency, and also has a reduced driving voltage and is thereby improved in device durability.
  • properties such as high efficiency, low driving voltage, and long lifetime can be achieved.
  • the arylamine compound of the present invention is characterized by having excellent electron blockability and high electron tolerance, being stable in a thin-film state, and being capable of confining excitons produced in the light-emitting layer.
  • an organic EL device having an electron blocking layer produced by using the present compound as an electron blocking material has a higher probability of electron-hole recombination, is reduced in thermal inactivation, and thus has high luminous efficiency. Further, the organic EL device is reduced in driving voltage and improved in current resistance, and thereby improved in maximum light emission luminance.
  • the arylamine compound of the present invention has excellent hole transportability and a wide band gap.
  • a dopant e.g., a fluorescent substance, a phosphorescent substance, or a delayed fluorescent substance
  • the driving voltage is reduced and luminous efficiency is improved.
  • the arylamine compound of the present invention is useful as a material for a hole injection layer, a hole transport layer, an electron blocking layer, or a light-emitting layer of an organic EL device, and can improve luminous efficiency, driving voltage, and durability of conventional organic EL devices.
  • the arylamine compound of the present invention is not only usable for organic EL devices, but also usable in the field of electronic devices, such as electrophotographic photoreceptors, image sensors, photoelectric conversion devices, solar cells, etc.
  • the arylamine compounds of the present invention are novel compounds, but these compounds can be synthesized according to known methods (see, for example, Patent Literature 5).
  • Figs. 1 to 12 illustrate concrete examples of preferred compounds among arylamine compounds represented by the general formula (1) that may be suitably used for the organic EL device of the present invention. Note, however, that the compounds are not limited to the illustrated compounds.
  • the arylamine compound represented by general formula (1) can be purified by known methods, such as column chromatography purification, adsorption purification with silica gel, activated carbon, activated clay, etc., recrystallization or crystallization using a solvent, sublimation purification, or the like.
  • Compound identification can be achieved by NMR analysis.
  • Physical properties to be measured may include such values as the melting point, glass transition point (Tg), work function, or the like.
  • the melting point serves as an index of vapor deposition characteristics.
  • the glass transition point (Tg) serves as an index of stability in a thin-film state.
  • the work function serves as an index of hole injectability, hole transportability, or electron blockability.
  • the melting point and glass transition point (Tg) can be measured, for example, with a high-sensitivity differential scanning calorimeter (DSC3100SA from Bruker AXS) using a powder.
  • DSC3100SA high-sensitivity differential scanning calorimeter
  • the work function can be found, for example, with an ionization potential measurement device (PYS-202 from Sumitomo Heavy Industries, Ltd.) by preparing a 100-nm thin film on an ITO substrate.
  • PYS-202 ionization potential measurement device
  • a structure of the organic EL device of the present invention may, for example, sequentially include, on a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode.
  • an electron blocking layer may be provided between the hole transport layer and the light-emitting layer, or a hole blocking layer may be provided between the light-emitting layer and the electron transport layer.
  • a single organic layer may have functions of several layers; for example, a single organic layer may have functions of the hole injection layer and the hole transport layer, or functions of the electron injection layer and the electron transport layer.
  • anode in the organic EL device of the present invention it is possible to use an electrode material having a large work function, such as ITO or gold.
  • an electrode material having a large work function such as ITO or gold.
  • the material for the hole injection layer in the organic EL device of the present invention it is possible to use: a porphyrin compound typified by copper phthalocyanine; a starburst triphenylamine derivative; an arylamine compound including, in its molecule, two or more triphenylamine structures or carbazolyl structures which are linked by a single bond or a divalent group containing no hetero atom; an acceptor heterocyclic compound such as hexacyanoazatriphenylene; or a coating-type polymer material.
  • These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.
  • a benzidine derivative such as N,N'-diphenyl-N,N'-di(m-tolyl)-benzidine (abbreviated hereinbelow as "TPD"), N,N'-diphenyl-N,N'-di( ⁇ -naphthyl)-benzidine (abbreviated hereinbelow as "NPD”), N,N,N',N'-tetrabiphenylylbenzidine, etc., or 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (abbreviated hereinbelow as "TAPC”), or an arylamine compound including, in its molecule, two or more triphenylamine structures or carbazolyl structures which are linked by a single bond or a divalent group containing no hetero
  • These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials.
  • a coating-type polymer material such as poly(3,4-ethylenedioxythiophene) (abbreviated hereinbelow as "PEDOT”)/poly(styrene sulfonate) (abbreviated hereinbelow as "PSS”).
  • PEDOT poly(3,4-ethylenedioxythiophene)
  • PSS poly(styrene sulfonate)
  • the hole injection layer or the hole transport layer it is possible to use: a material ordinarily used for such layers and p-doped with, for example, trisbromophenylamine hexachloroantimonate or a radialene derivative (see, for example, Patent Literature 6); or a polymer compound having, as a partial structure thereof, a benzidine derivative structure such as TPD.
  • a material ordinarily used for such layers and p-doped with, for example, trisbromophenylamine hexachloroantimonate or a radialene derivative see, for example, Patent Literature 6
  • a polymer compound having, as a partial structure thereof, a benzidine derivative structure such as TPD.
  • a compound having an electron blocking action such as: a carbazole derivative, such as 4,4',4"-tri(N-carbazolyl)triphenylamine (abbreviated hereinbelow as "TCTA”), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (abbreviated hereinbelow as "mCP”), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (abbreviated hereinbelow as "Ad-Cz”), etc.; or a compound containing a triarylamine structure and a triphenylsilyl group typified by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phen
  • These materials may also serve as a material for the hole transport layer. These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials. These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.
  • the material for the light-emitting layer in the organic EL device of the present invention it is possible to use, other than the arylamine compound of the present invention, one of various metal complexes such as a metal complex of a quinolinol derivative, e.g., Alq 3 , an anthracene derivative, a bisstyrylbenzene derivative, a pyrene derivative, an oxazole derivative, a poly(para-phenylene vinylene) derivative, etc.
  • the light-emitting layer may be constituted by a host material and a dopant material.
  • an anthracene derivative may preferably be used, and also, in addition to such light-emitting materials as the arylamine compound of the present invention, it is possible to use, for example, a heterocyclic compound having an indole ring as a partial structure of a fused ring, a heterocyclic compound having a carbazole ring as a partial structure of a fused ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, etc.
  • the dopant material it is possible to use quinacridone, coumarin, rubrene, perylene, a derivative of the above, a benzopyran derivative, a rhodamine derivative, an aminostyryl derivative, etc.
  • These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials.
  • These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.
  • a phosphorescent substance for the light-emitting material.
  • a phosphorescent substance such as a metal complex of iridium, platinum, etc. Examples may include green phosphorescent substances such as Ir(ppy) 3 etc., blue phosphorescent substances such as FIrpic, FIr6, etc., and red phosphorescent substances such as Btp 2 Ir(acac) etc.
  • examples of the hole injecting/transporting host material may include a carbazole derivative such as 4,4'-di(N-carbazolyl)biphenyl (abbreviated hereinbelow as "CBP"), TCTA, mCP, etc., as well as the arylamine compound of the present invention.
  • examples of the electron-transporting host material may include p-bis(triphenylsilyl)benzene (abbreviated hereinbelow as "UGH2”), 2,2',2"-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (abbreviated hereinbelow as "TPBI”), etc.
  • doping of the host material(s) with a phosphorescent substance is preferably performed by co-vapor deposition within a range of 1 to 30 wt.% with respect to the entire light-emitting layer.
  • the light-emitting material it is possible to use a material emitting delayed fluorescence, e.g., PIC-TRZ, CC2TA, PXZ-TRZ, a CDCB derivative such as 4CzIPN, etc. (see, for example, Non-Patent Literature 3).
  • a material emitting delayed fluorescence e.g., PIC-TRZ, CC2TA, PXZ-TRZ, a CDCB derivative such as 4CzIPN, etc.
  • the material for the hole blocking layer in the organic EL device of the present invention it is possible to use a compound having a hole blocking action, with examples including phenanthroline derivatives such as bathocuproine (abbreviated hereinbelow as "BCP"), metal complexes of a quinolinol derivative such as BAlq, various rare-earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, etc. These materials may also serve as materials for the electron transport layer. These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer.
  • phenanthroline derivatives such as bathocuproine (abbreviated hereinbelow as "BCP")
  • metal complexes of a quinolinol derivative such as BAlq
  • various rare-earth complexes such as BAlq
  • oxazole derivatives such as BAlq
  • a laminate structure constituted by layers each formed singly by the respective materials or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials.
  • These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.
  • a metal complex of a quinolinol derivative such as Alq 3 , BAlq, etc., one of various metal complexes, a triazole derivative, a triazine derivative, an oxadiazole derivative, a pyridine derivative, a pyrimidine derivative, a benzimidazole derivative, a thiadiazole derivative, an anthracene derivative, a carbodiimide derivative, a quinoxaline derivative, a pyridoindole derivative, a phenanthroline derivative, a silole derivative, etc.
  • a quinolinol derivative such as Alq 3 , BAlq, etc.
  • These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials. These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.
  • an alkali metal salt such as lithium fluoride, cesium fluoride, etc., an alkaline-earth metal salt such as magnesium fluoride etc., a metal complex of a quinolinol derivative such as quinolinol lithium etc., a metal oxide such as aluminum oxide etc., or a metal such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), cesium (Cs), etc.
  • the electron injection layer may, however, be omitted by suitable selection of the electron transport layer and the cathode.
  • the electron injection layer and the electron transport layer it is possible to use a material ordinarily used for such layers and n-doped with a metal such as cesium etc.
  • a metal having a low work function such as aluminum etc., or an alloy having an even lower work function, such as magnesium silver alloy, magnesium indium alloy, aluminum magnesium alloy, etc., may be used as the electrode material.
  • a reaction vessel was charged with 7.0 g of 2,4,6-triphenyl-bromobenzene, 12.4 g of bis(biphenyl-4-yl)-[3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.3 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 3.6 g of sodium hydrogen carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of THF/H 2 O. After the mixture was allowed to cool, ethyl acetate/H 2 O was added into the system.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of 2,4,6-triphenyl-bromobenzene, 22.3 g of (biphenyl-4-yl)-(4-naphthalen-1-yl-phenyl)-[3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.4 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 5.1 g of sodium hydrogen carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of THF/H 2 O.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 11.0 g of 2,4,6-triphenyl-bromobenzene, 24.6 g of (biphenyl-4-yl)-(4-naphthalen-2-yl-phenyl)-[3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.5 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 5.6 g of sodium hydrogen carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of THF/H 2 O.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 13.7 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(4-phenanthren-9-yl-phenyl)-amine, 4.0 g of bromobenzene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.1 g of sodium t-butoxide, and the mixture was stirred under reflux for 6 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-phenyl-amine, 7.8 g of 4-bromo-[1,1':4',1"]terphenyl, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 3.0 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 12.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-phenyl-amine, 10.0 g of 1-(4'-bromo-biphenyl-4-yl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.9 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 12.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-phenyl-amine, 10.0 g of 2-(4'-bromo-biphenyl-4-yl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.9 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of 2,4,6-triphenyl-bromobenzene, 18.5 g of (biphenyl-4-yl)-(phenanthren-9-yl)-[3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.4 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 5.1 g of sodium hydrogen carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of THF/H 2 O.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a reaction vessel was charged with 13.4 g of (4-naphthalen-2-yl-phenyl)-(3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-amine, 7.6 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.3 g of sodium t-butoxide, and the mixture was stirred under reflux for 6 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 7.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-amine, 11.0 g of 2-(4-bromo-phenyl)-naphthalene, 0.6 g of tris(dibenzylideneacetone)dipalladium(0), 4.4 g of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and 6.8 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 7.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-amine, 11.0 g of 1-(4-bromo-phenyl)-naphthalene, 0.6 g of tris(dibenzylideneacetone)dipalladium(0), 4.4 g of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and 6.8 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 13.4 g of (4-naphthalen-2-yl-phenyl)-(3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-amine, 6.9 g of 9-bromo-phenanthrene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.3 g of sodium t-butoxide, and the mixture was stirred under reflux for 6 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a reaction vessel was charged with 7.5 g of 2,4,6-triphenyl-bromobenzene, 12.2 g of (biphenyl-4-yl)-phenyl-[3'-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-biphenyl-4-yl]-amine, 0.5 g of tetrakis(triphenylphosphine)palladium(0), and 4.0 g of potassium carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of toluene/EtOH/H 2 O. After the mixture was allowed to cool, ethyl acetate/H 2 O was added into the system.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of (3',5'-diphenyl-1,1':2',1":3"-1′′′-quaterphenyl-4"'-yl)-phenyl-amine, 5.7 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of (3',5'-diphenyl-1,1':2',1":3"-1′′′-quaterphenyl-4"'-yl)-phenyl-amine, 6.2 g of 2-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 11.0 g of (3',5'-diphenyl-1,1':2',1":3"-1′′′-quaterphenyl-4"'-yl)-phenyl-amine, 8.0 g of 9-(4-bromo-phenyl)-phenanthrene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of (3',5'-diphenyl-1,1':2',1":3"-1′′′-quaterphenyl-4"'-yl)-phenyl-amine, 6.7 g of 4-bromo-[1,1':4',1"]terphenyl, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-4′′′-quaterphenyl-4′′′-yl)-amine, 4.5 g of 4-bromo-biphenyl, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.0 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-1′′′-quaterphenyl-4′′′-yl)-amine, 5.4 g of 2-(4-bromo-phenyl)-naphthalene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.0 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-1′′′-quaterphenyl-4′′′-yl)-amine, 5.4 g of 1-(4-bromo-phenyl)-naphthalene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-4′′′-quaterphenyl-4′′′-yl)-amine, 4.9 g of 2-bromo-phenanthrene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3',5'-diphenyl-1,1':2',1":3"-4′′′-quaterphenyl-4′′′-yl)-amine, 4.9 g of 9-bromo-phenanthrene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a reaction vessel was charged with 10.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-phenyl-amine, 9.5 g of 9-(4'-bromo-biphenyl-4-yl)-phenanthrene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.4 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 12.5 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(4-phenanthren-9-yl-phenyl)-amine, 5.4 g of 4-bromo-biphenyl, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 3.7 g of sodium t-butoxide, and the mixture was stirred under reflux for 6 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 8.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(1,1':4',1"-terphenyl-4-yl)-amine, 4.3 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 8.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(1,1':4',1"-terphenyl-4-yl)-amine, 4.0 g of 2-(4-bromo-phenyl)-naphthalene, 0.1 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-t-butylphosphine, and 1.5 g of sodium t-butoxide, and the mixture was stirred under reflux for 3 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-red powder was identified by NMR.
  • a reaction vessel was charged with 8.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(1,1':4',1"-terphenyl-4-yl)-amine, 4.3 g of 1-(3-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the obtained crude product was purified by crystallization with a toluene/acetone/n-heptane mixed solvent, to obtain 6.0 g of a white powder of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(3-naphthalen-1-yl-phenyl)-(1,1':4',1"-terphenyl-4-yl)-amine (Compound (134)) (yield: 56.6%).
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 8.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(1,1':4',1"-terphenyl-4-yl)-amine, 4.3 g of 2-(3-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained white powder was identified by NMR.
  • a reaction vessel was charged with 8.0 g of (3',5'-diphenyl-1,1':2',1"-terphenyl-3"-yl)-(1,1':4',1"-terphenyl-4-yl)-amine, 4.3 g of 1-(2-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.5 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product.
  • the structure of the obtained pale-yellow powder was identified by NMR.
  • a 100-nm-thick vapor deposition film was formed on an ITO substrate by using the respective arylamine compounds obtained in Examples 1 to 27, and the work function was measured using an ionization potential measurement device (PYS-202 from Sumitomo Heavy Industries, Ltd.). The results are shown in Table 2.
  • an organic EL device was prepared by vapor-depositing a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a capping layer 10 in this order onto a glass substrate 1 having formed thereon a reflective ITO electrode as a transparent anode 2 in advance.
  • a glass substrate 1 having formed thereon, in order, a 50-nm-thick ITO film, a 100-nm-thick silver-alloy reflective film, and a 5-nm-thick ITO film was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried for 10 minutes on a hot plate heated to 250°C. Then, after UV ozone treatment for 2 minutes, the glass substrate having the ITO was mounted to a vacuum vapor deposition apparatus, in which the pressure was reduced to 0.001 Pa or lower.
  • a hole injection layer 3 was formed so as to cover the transparent anode 2 and so that the film thickness was 10 nm, by performing binary vapor deposition of an electron acceptor (Acceptor-1) having the following structural formula and a compound (HTM-1) having the following structural formula at a rate at which the vapor deposition rate ratio between Acceptor-1 and HTM-1 was 3:97.
  • an electron acceptor (Acceptor-1) having the following structural formula
  • HTM-1) having the following structural formula at a rate at which the vapor deposition rate ratio between Acceptor-1 and HTM-1 was 3:97.
  • the compound (HTM-1) having the following structural formula was formed as a hole transport layer 4 having a film thickness of 140 nm.
  • Compound (58) of Example 1 was formed as an electron blocking layer 5 having a film thickness of 5 nm.
  • a light-emitting layer 6 was formed so that the film thickness was 20 nm, by performing binary vapor deposition of a compound (EMD-1) having the following structural formula and a compound (EMH-1) having the following structural formula at a rate at which the vapor deposition rate ratio between EMD-1 and EMH-1 was 5:95.
  • an electron transport layer 7 was formed so that the film thickness was 30 nm, by performing binary vapor deposition of a compound (ETM-1) having the following structural formula and a compound (ETM-2) having the following structural formula at a rate at which the vapor deposition rate ratio between ETM-1 and ETM-2 was 50:50.
  • lithium fluoride was formed as an electron injection layer 8 having a film thickness of 1 nm.
  • a magnesium-silver alloy was formed as a cathode 9 having a film thickness of 12 nm.
  • CPL-1 having the following structure was formed as a capping layer 10 having a film thickness of 60 nm.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (59) of Example 2 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (60) of Example 3 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (15) of Example 4 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (31) of Example 5 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (32) of Example 6 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (33) of Example 7 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (61) of Example 8 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (76) of Example 9 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (77) of Example 10 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (78) of Example 11 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (79) of Example 12 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (96) of Example 13 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (100) of Example 14 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (101) of Example 15 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (102) of Example 16 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (107) of Example 17 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (115) of Example 18 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (116) of Example 19 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (117) of Example 20 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (118) of Example 21 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (119) of Example 22 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (127) of Example 23 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (130) of Example 24 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (132) of Example 25 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (133) of Example 26 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (134) of Example 27 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (135) of Example 28 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (136) of Example 29 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • Example 32 For comparison, an organic EL device was produced according to the same conditions, except that, in Example 32, a compound (HTM-2) having the following structural formula (see, for example, Patent Literature 5) was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5.
  • Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • Example 32 For comparison, an organic EL device was produced according to the same conditions, except that, in Example 32, a compound (HTM-3) having the following structural formula was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.
  • Device life was measured using the organic EL devices produced in Examples 32 to 60 and Comparative Examples 1 and 2. The results are collectively shown in Table 3. Device life was measured as follows. Constant current driving was performed, with the light emission luminance at the start of light emission (i.e., initial luminance) being 1000 cd/m 2 , and the time it took for the light emission luminance to attenuate to 950 cd/m 2 (95% attenuation: amounting to 95% when the initial luminance is considered 100%) was measured.
  • the organic EL devices employing the arylamine compounds of the present invention have low driving voltages. Further, while the luminous efficiency when a current having a current density of 10 mA/cm 2 was passed was 8.97 to 9.15 cd/A for the organic EL devices of Comparative Examples 1 and 2, the organic EL devices of Examples 32 to 60 had high efficiency of 9.37 to 11.05 cd/A. Furthermore, while the organic EL devices of Comparative Examples 1 and 2 had a power efficiency of 8.19 to 8.23 lm/W, the organic EL devices of Examples 32 to 60 had high efficiency of 8.51 to 9.95 lm/W. Furthermore, while the organic EL devices of Comparative Examples 1 and 2 had a device life (95% attenuation) of 245 to 269 hours, the organic EL devices of Examples 32 to 60 had comparable or longer lifetime of 267 to 632 hours.
  • the organic EL device according to the present invention which uses an arylamine compound having a specific structure, has improved luminous efficiency, and also, the organic EL device can be improved in durability. Thus, for example, application can be expanded to home electrical appliances and lightings. Further, the arylamine compound of the present invention is not only usable for organic EL devices, but also usable in the field of electronic devices, such as electrophotographic photoreceptors, image sensors, photoelectric conversion devices, solar cells, etc.
EP21744716.8A 2020-01-21 2021-01-20 Arylaminverbindung und organisches elektrolumineszenzelement Pending EP4095124A4 (de)

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DE69412567T2 (de) 1993-11-01 1999-02-04 Hodogaya Chemical Co Ltd Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung
EP0666298A3 (de) 1994-02-08 1995-11-15 Tdk Corp Organisches elektrolumineszentes Element und darin gebrauchte Verbindung.
JP5010076B2 (ja) * 2001-08-01 2012-08-29 三井化学株式会社 有機電界発光素子
KR100787425B1 (ko) 2004-11-29 2007-12-26 삼성에스디아이 주식회사 페닐카바졸계 화합물 및 이를 이용한 유기 전계 발광 소자
WO2005115970A1 (ja) 2004-05-25 2005-12-08 Hodogaya Chemical Co., Ltd. ｐ－ターフェニル化合物および該化合物を用いた電子写真用感光体
JP2009170810A (ja) * 2008-01-18 2009-07-30 Mitsui Chemicals Inc 有機電界発光素子
EP2449054A4 (de) * 2009-07-01 2013-05-29 Du Pont Chrysenverbindungen für leuchtanwendungen
EP2684932B8 (de) 2012-07-09 2016-12-21 Hodogaya Chemical Co., Ltd. Diarylamino matrix material dotiert mit einer mesomeren radialenverbindung
WO2016199743A1 (ja) 2015-06-11 2016-12-15 保土谷化学工業株式会社 アリールアミン化合物および有機エレクトロルミネッセンス素子
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